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"Shoulda. Coulda. Woulda."
A successful author is forced to confront an unrequited high school crush when he returns home to deliver a commencement address to graduating seniors. Shasta O'Neil, a sexy high school senior flirts with the visiting author and invites him to the prom.
47 Cast Members
Winona Ryder
Scarlet Smith
Mark Polish
Henry McCarthy
Sean Astin
Big Girl
Hilary Duff
Shasta O'Neil
Josh Holloway
Wino
Jon Cryer
Javier
Chevy Chase
Principal Marshall
Jessica St. Clair
Darcy Portola
Frances Conroy
Mrs. Leuchtenberger
Marc Blucas
Brad Nelson
Joanna Cassidy
Mrs. Smith
Dee Wallace
Mrs. McCarthy
Michael Gross
Mr. McCarthy
Ken Johnson
Mr. O'Neil
Jessica Schatz
Mrs. O'Neil
Scott Michael Campbell
Officer Bird
Blake Adams
Cop
Catherine Black
Goth Girl
Jenn Shagrin
Jungle Journalist #1
Josh Sussman
Jungle Journalist #2
